Anthracene derivative and a process of preparing it



' acetylchloride and having'the following probable Patented Aug. 20,1935 UNITED STATES atlases Par ENiT OFFICE ANTHR'ACENE DERIVATIVE AND APROCESS 0F PREPARING-I1 Wilhelm Eckert: and Walter- Gmelin, Frankfort--V on-theeMain-Hochst, Germany, assignors to GeneralAniline Works, Inc.,New York, N. Y.,,a corporation of Delaware No Drawing.

Application June 30, 1931, Serial.

No. 548,028. In Germany August 22, 1930 8 Claims.

Our present invention relatesto new anthracene derivatives and a processof preparing them.

We have 'found that new anthracene derivatives are obtainable in asmooth reaction and with a verygood yield bytreating with aluminiumchloride, in the presence or absence of a solvent or diluent, attemperatures not exceeding 100 C.,

the products obtainable by condensing according to known methods (of,for instance, German Patents 492,247, $93,688 and49ao5-1) 'antracene,

or a substitution product thereof, with chlorformula:

- oo-onzol wherein X means hydrogen or a substituent of the groupconsisting of halogen and-alkyl. The anthracene derivatives obtainableaccording to our new process are valuableintermediateproducts forthemanufacture of dyestuffs. They are feebly yellow colored products,dissolve in concentrated sulfuric acid'to.- an orange-yellow solutionshowing a greenish fluorescence and correspond with the probable generalformula:

wherein X stands for hydrogen, alkyl o r halogen. It is also possiblethat condensation products of the following general formula areobtained.

1) 10 parts of the chloracetylanthracene obtainable by condensation of"anthracene with chloracetylchloride and corresponding with the followingprobable iormula:

are thoroughly mixed with about 40- parts of aluminium chloride and 10parts of sodium chloride and the whole is cautiously heated to about 15C. A vivid reaction sets in and the temperature rises to about C.Thereupon, the melt is introducedinto ice, the whole'is boiled for ashort time, filtered with suction and the solid matter is washed anddried. 20

The reaction product thus obtained probably has the followingconstitution:

, :ocr nn It crystallizes, for instance, from benzene in the form ofyellow prisms melting at 151 C.-l52 C. It dissolves in concentratedsulfuric acid to a yellowish orange solution showing a greenishfluorescence, whereas the starting material dissolves in concentratedsulfuric acid to a deep red solution; i

' (2) By starting from the product, obtainable from 2-methylanthraceneand chloracetylchloride and proceeding as in Example 1, there is 013- 4atained the corresponding ketone of 2-methylan thracene of the followingprobable constitution:

o GCH2 I OHs 45 The crude product, for instance, maybedissolvedandreprecipitatedfrom alcohol. It crystallizes in yellow prisms meltingat 127 C; it dissolves easily, for instance, in benzene. In concentratedsulfuric acid it dissolves to an orange yellow solution showing ayellowish green fluorescence. 55

solves in sulfuric acid to an orange yellow solu- The reaction tionshowing a green fluorescence. temperature is advantageously not allowedto exceed 40 C. The product is isolated by addition of water to themelt, the chlorobenzene is distilled off by means of steam and theresidue is recrystallized from alcohol. The product which has theprobable constitution:

crystallizes in the form of yellow prisms melting at 165 C; it dissolveseasily in benzene. In concentrated sulfuric acid it dissolves to anorange yellow solution having a yellowish green fluorescence.

As hereinbefore stated, there is a possibility that our new products,whose preparation and properties we have fully described, actuallypossess structural formulae which are slightly different from thoseemployed in the appended product claims. However, although we have beenunable to conclusively determine that these structural formulae arecorrect, they do to the best of our present knowledge and beliefcorrectly represent the new products obtainable by the new processherein described and claimed.

We claim:

1. The process which comprises treating with aluminium chloride at atemperature not exceeding C. a compound obtainable by condensing ananthracene compound with chloroacetylchloride and having the probablegeneral formula:

wherein X means hydrogen or a substituent of the group consisting ofhalogen and alkyl.

2. The process which comprises treating with aluminium chloride in thepresence of sodium chloride at a temperature of about 60 C. to about 100C.a compound obtainable by condensing anthracene withohloracetylchloride and having the probable formula:

3. The process which comprises treating with aluminium chloride at atemperature of about 60C. to about 100 C. a compound obtainable bycondensing 2-methylanthracene with chloracetylchloride and having theprobable formula:

I W 0V0 4. The process which comprises treating with aluminium chloridein the presence of chloroben-- zene at a temperature of about 0 C. to'about 10 C. a compound obtainable by condensing fichloranthracene withchloracetylchloride and having the probable formula:

5. The compounds ofthe general formula:

oo-oHz wherein X stands for hydrogen, alkyl or halogen said productshaving a feebly yellow color and dissolving in concentrated. sulfuricacid to an orange-yellowsolution showing a greenish fluorescence.

6. The compound of 'the formula:

said product crystallizing from benzene in the: form of yellow prismsmelting at 151- C.- 152 C. and dissolving inconcentrated sulfuric acidto a yellowish orange solution showing-'- a greenish fluorescence. v

7. The compound of'the formula:

crystalli'zing in'yellow prisms melting at 0., easily soluble .inbenzene and dissolving in con centrated sulfuric acid to an orangeyellow solu' tion showing a yellowish green fluorescence.

WILHELM ECKERT. WALTER GMELIN.

